US6011142A - 5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials - Google Patents

5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials Download PDF

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Publication number
US6011142A
US6011142A US09/051,378 US5137898A US6011142A US 6011142 A US6011142 A US 6011142A US 5137898 A US5137898 A US 5137898A US 6011142 A US6011142 A US 6011142A
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formula
compound
methyl
preparation
product
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Inventor
Alain Bonnet
Bernadette Chappert
Jacques Lagouardat
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Aventis Pharma SA
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Hoechst Marion Roussel
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Priority to US09/772,277 priority Critical patent/USRE38426E1/en
Assigned to HOECHST MARION ROUSSEL reassignment HOECHST MARION ROUSSEL ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: CHAPPERT, B., BONNET, A., LAGOUARDAT, J.
Application granted granted Critical
Publication of US6011142A publication Critical patent/US6011142A/en
Assigned to AVENTIS PHARMA S.A. reassignment AVENTIS PHARMA S.A. MERGER (SEE DOCUMENT FOR DETAILS). Assignors: ROUSSEL, HOECHST MARION
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
    • C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
    • C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals

Definitions

  • the present invention relates to new derivatives of 5-O-desosaminyl 6-O-methyl erythronolide A, their preparation process and their use in the preparation of biologically active products.
  • a subject of the invention is the compounds of formula (I): ##STR2## in which R represents a carboxylic acid remainder containing up to 18 carbon atoms.
  • carboxylic acid remainders there can in particular be mentioned the acetyl, propionyl, butyryl, isobutyryl, n-valeryl, isovaleryl, tert-valeryl and pivalyl radicals.
  • a more particular subject of the invention is the compounds of formula (I) in which R represents an acetyl radical.
  • a subject of the invention is also a preparation process characterized in that a compound of formula (II): ##STR3## in which R retains its previous meaning, is subjected to the action of an agent capable of selectively activating the hydroxyl in position 11, then to the action of a base to obtain the compound of formula (III): ##STR4## which is subjected to the action of carbonyldiimidazole, then to the action of the hydrazine NH 2 NH 2 to obtain the corresponding compound of formula (I).
  • the compounds of formula (II) are known in a general way and can be prepared according to the process described in European Patent Application 619319.
  • the agent capable of selectively activating the hydroxyl in position 11 is a sulphonic acid derivative such as methanesulphonic, paratoluenesulphonic, trifluoromethanesulphonic anhydride or thionyl chloride SOCl 2 , which forms a cyclic sulphite with the OH function in position 12,
  • the base used to produce a 10(11) double bond is a diazabicycloundecene, for example DBU (or 1,8-diazabicyclo-[5-4-0]undec-7-ene), or DBN (or 1,5-diazabicyclo[4,3,0]non-5-ene or 2,6-lutidine, or 2,4,6-collidine or tetramethyl-guanidine,
  • DBU diazabicycloundecene
  • DBN or 1,5-diazabicyclo[4,3,0]non-5-ene or 2,6-lutidine, or 2,4,6-collidine or tetramethyl-guanidine
  • reaction of the compound of formula (III) with carbonyldiimidazole takes place in the presence of one of the bases mentioned above or also in the presence of sodium hydride, triethylamine, sodium or potassium carbonate or bicarbonate, NaN(SiMe 3 ) 2 or LiN(SiMe 3 ) 2 ,
  • the hydrazine is used in the form of hydrazine hydrate.
  • the subject of the invention is therefore, as chemical products, the compounds of formula (III) and quite particularly the compound of formula (III) in which R represents an acetyl radical.
  • the compounds of formula (I) are useful intermediate products which can in particular lead to the preparation of antibiotic products, described and claimed in European Patent Application 0,676,409.
  • a subject of the invention is the use, characterised in that a compound of formula (I) is subjected to the action of a cleaving agent of the protected hydroxyl functions to obtain the compound of formula (IV): ##STR5## which is subjected to the action of an aldehyde of formula (V): ##STR6## in which R' 1 represents a hydrogen atom or a saturated or unsaturated hydrocarbon radical containing up to 23 carbon atoms, optionally interrupted by one or more heteroatoms and optionally having one or more functional groups, to obtain the compound of formula (VI): ##STR7## which is subjected to the action of an oxidizing agent of the hydroxyl in position 3 then to the action of a cleaving agent of the hydroxyl in position 2' to obtain the compound of formula (VII): ##STR8## which is subjected to the action of a reducing agent to obtain the corresponding compound of formula (VIII): ##STR9## in which R' 1 retains its previous
  • R' 1 represen ts the radical ##STR10## cleavage of the protected hydroxyl functions is carried out by saponification then acidification of the ester function,
  • oxidation of the hydroxyl in position 3 is carried out using a diimide in the presence of DMSO, for example the hydrochloride of 1-ethyl 3-(3-dimethylamino propyl) carbodiimide,
  • the reducing agent is NaBH 3 CN or NaBH(OAc) 3 or also NaBH 4 in the presence of acetic acid or hydrogen in the presence of a catalyst such as palladium, platinum and optionally in the presence of an acid such as hydrochloric acid or acetic acid.
  • the products of formula (VII) are products having useful antibiotic properties, described and claimed in European Patent 0,676,409.
  • a mixture of 10.7 g of this product and 124 ml of dimethyl-formamide is agitated at 50° C. 2.53 ml of DBU is added over 5 minutes. Agitation is carried out for 48 hours at 50° C., and the mixture is then poured into water. 100 cm 3 of ethyl acetate is added. Decantation is carried out, and the resultant product is washed with water (1.25 1), extracted with ethyl acetate (400 ml) and dried over magnesium sulphate, then filtered and the filtrate is evaporated to dryness. Approximately 50 ml of isopropyl ether is added, and the imixture is left to crystallize for 72 hours, filtered, rinsed and dried. 5.514 g of desired product, which melts at 174° C., is obtained.
  • a mixture containing 2.623 g of product prepared in the preceding stage, 972 mg of carbonyldiimidazole, 30 ml of dichloromethane and 60 ⁇ l of DBU is agitated. Agitation is maintained for 4 hours. 404 ⁇ l of hydrazine hydrate is added. Agitation is carried out for 24 hours, and 50 ml of 0.5 M sodium acid phosphate is added. The mixture is decanted and the resultant product is extracted with methylene chloride and dried. The product is taken up in isopropyl ether. The mixture is left to crystallize overnight. Filtration, rinsing with isopropyl ether and drying are carried out. 2.415 g of desired product is obtained.
  • the product is chromatographed on silica, eluting with an ethyl acetate-triethylamine (9-1) mixture. 647 mg of product is collected. A mixture of 566 mg of this product and 18 ml of methanol is maintained under agitation overnight and 540 mg of desired product is obtained.
  • 0.38 g of product prepared in the preceding stage and 38 mg of platinum oxide are dissolved in 10 ml of ethyl acetate. Hydrogenation is carried out for 24 hours under vigourous agitation. The mixture is filtered, rinsed with ethyl acetate and evaporated under reduced pressure. 0.375 g of product is obtained, which is taken up in 5 ml of methanol, 175 ⁇ l of acetic acid and 90 mg of sodium borohydride. Agitation is carried out for 3 hours at ambient temperature. The methanol is driven off and the product is taken up in a methylene chloride-water mixture. The pH is adjusted to 8-9 with a 28% ammonium hydroxide solution.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
US09/051,378 1995-10-09 1996-10-08 5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials Ceased US6011142A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
US09/772,277 USRE38426E1 (en) 1995-10-09 1996-10-08 5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR9511861A FR2739620B1 (fr) 1995-10-09 1995-10-09 Nouveaux derives de la 5-0-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs
FR9511861 1995-10-09
PCT/FR1996/001567 WO1997013774A2 (fr) 1995-10-09 1996-10-08 Nouveaux derives de la 5-o-desosaminyl 6-o-methyl erythronolide a, leur procede de preparation et leur application a la preparation de produits biologiquement actifs

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US09/772,277 Reissue USRE38426E1 (en) 1995-10-09 1996-10-08 5-O-deosaminyl 6-O-methyl erythronolide A derivatives, preparation method therefor and use thereof for preparing biologically active materials

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US6011142A true US6011142A (en) 2000-01-04

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US (1) US6011142A (cs)
EP (1) EP0854879B1 (cs)
JP (1) JP4327248B2 (cs)
KR (1) KR100451063B1 (cs)
CN (1) CN1067401C (cs)
AP (1) AP888A (cs)
AR (1) AR004688A1 (cs)
AT (1) ATE212034T1 (cs)
AU (1) AU708351B2 (cs)
BG (1) BG63752B1 (cs)
BR (1) BR9610959A (cs)
CA (1) CA2231562C (cs)
CZ (1) CZ293430B6 (cs)
DE (1) DE69618607T2 (cs)
DK (1) DK0854879T3 (cs)
EA (1) EA000765B1 (cs)
EE (1) EE03878B1 (cs)
ES (1) ES2171722T3 (cs)
FR (1) FR2739620B1 (cs)
GE (1) GEP20032899B (cs)
HU (1) HUP9900136A3 (cs)
IL (1) IL123613A0 (cs)
MX (1) MX9802655A (cs)
NO (1) NO312592B1 (cs)
PL (1) PL183645B1 (cs)
PT (1) PT854879E (cs)
RO (1) RO118874B1 (cs)
SI (1) SI0854879T1 (cs)
SK (1) SK283619B6 (cs)
TR (1) TR199800624T1 (cs)
UA (1) UA52621C2 (cs)
WO (1) WO1997013774A2 (cs)
ZA (1) ZA966666B (cs)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399582B1 (en) 1999-04-16 2002-06-04 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
WO2002050092A1 (en) * 2000-12-21 2002-06-27 Glaxo Group Limited Macrolide antibiotics
US6590083B1 (en) 1999-04-16 2003-07-08 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
US20060100164A1 (en) * 2003-03-10 2006-05-11 Chang-Hsing Liang Novel antibacterial agents
US20100216731A1 (en) * 2007-10-25 2010-08-26 Cempra Pharmaceuticals, Inc. Process for the preparation of macrolide antibacterial agents
US20110195920A1 (en) * 2008-10-24 2011-08-11 Cempra Pharmaceuticals, Inc. Biodefenses using triazole-containing macrolides
US8759500B2 (en) 2010-03-22 2014-06-24 Cempra Pharmaceuticals, Inc. Crystalline forms of a macrolide, and uses therefor
US9051346B2 (en) 2010-05-20 2015-06-09 Cempra Pharmaceuticals, Inc. Process for preparing triazole-containing ketolide antibiotics
US9480679B2 (en) 2009-09-10 2016-11-01 Cempra Pharmaceuticals, Inc. Methods for treating malaria, tuberculosis and MAC diseases
US9751908B2 (en) 2013-03-15 2017-09-05 Cempra Pharmaceuticals, Inc. Convergent processes for preparing macrolide antibacterial agents
US9815863B2 (en) 2010-09-10 2017-11-14 Cempra Pharmaceuticals, Inc. Hydrogen bond forming fluoro ketolides for treating diseases
US9861616B2 (en) 2013-03-14 2018-01-09 Cempra Pharmaceuticals, Inc. Methods for treating respiratory diseases and formulations therefor
US9937194B1 (en) 2009-06-12 2018-04-10 Cempra Pharmaceuticals, Inc. Compounds and methods for treating inflammatory diseases
US10188674B2 (en) 2012-03-27 2019-01-29 Cempra Pharmaceuticals, Inc. Parenteral formulations for administering macrolide antibiotics

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2777282B1 (fr) * 1998-04-08 2001-04-20 Hoechst Marion Roussel Inc Nouveaux derives de la 2-fluoro 3-de((2,6-dideoxy 3-c-methyl 3-0-methyl-alpha-l-ribohexopyranosyl) oxyl) 6-o-methyl 3-oxo erythromycine, leur procede de preparation et leur application a la synthese de principes actifs de medicaments
ATE340183T1 (de) * 1999-04-16 2006-10-15 Kosan Biosciences Inc Antiinfektiöse makrolidderivate

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US3923784A (en) * 1973-09-10 1975-12-02 Hoffmann La Roche Erythromycin a derivatives
US4518590A (en) * 1984-04-13 1985-05-21 Pfizer Inc. 9α-Aza-9α-homoerythromycin compounds, pharmaceutical compositions and therapeutic method
US4742049A (en) * 1986-06-04 1988-05-03 Abbott Laboratories Semisynthetic erythromycin antibiotics
US4921839A (en) * 1987-02-24 1990-05-01 Beecham Group P.L.C. Erythromycin a 11,12-carbonate 9-oxime derivatives
EP0619320A1 (en) * 1991-12-27 1994-10-12 Taisho Pharmaceutical Co. Ltd 5-o-desosaminylerythronolide derivative
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EP0682038A1 (en) * 1993-01-26 1995-11-15 Taisho Pharmaceutical Co. Ltd 5-o-desosaminylerythronolide derivative

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US4742049A (en) * 1986-06-04 1988-05-03 Abbott Laboratories Semisynthetic erythromycin antibiotics
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Cited By (33)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399582B1 (en) 1999-04-16 2002-06-04 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
US6458771B1 (en) 1999-04-16 2002-10-01 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
US6590083B1 (en) 1999-04-16 2003-07-08 Ortho-Mcneil Pharmaceutical, Inc. Ketolide antibacterials
WO2002050092A1 (en) * 2000-12-21 2002-06-27 Glaxo Group Limited Macrolide antibiotics
US20040082526A1 (en) * 2000-12-21 2004-04-29 Daniele Andreotti Macrolide antibiotics
US6900183B2 (en) 2000-12-21 2005-05-31 Glaxo Group Limited Macrolide antibiotics
US20060100164A1 (en) * 2003-03-10 2006-05-11 Chang-Hsing Liang Novel antibacterial agents
US20090209593A1 (en) * 2003-03-10 2009-08-20 Chang-Hsing Liang Novel antibacterial agents
US7601695B2 (en) 2003-03-10 2009-10-13 Optimer Pharmaceuticals, Inc. Antibacterial agents
US8012943B2 (en) 2003-03-10 2011-09-06 Optimer Pharmaceuticals, Inc. Antibacterial agents
US9200026B2 (en) 2003-03-10 2015-12-01 Merck Sharp & Dohme Corp. Antibacterial agents
US8343936B2 (en) 2003-03-10 2013-01-01 Optimer Pharmaceuticals, Inc. Antibacterial agents
US20100216731A1 (en) * 2007-10-25 2010-08-26 Cempra Pharmaceuticals, Inc. Process for the preparation of macrolide antibacterial agents
US10131684B2 (en) 2007-10-25 2018-11-20 Cempra Pharmaceuticals, Inc. Process for the preparation of macrolide antibacterial agents
US9453042B2 (en) 2007-10-25 2016-09-27 Cempra Pharmaceuticals, Inc. Process for the preparation of macrolide antibacterial agents
US8791080B2 (en) 2008-10-24 2014-07-29 Cempra Pharmaceuticals, Inc. Methods for treating gastrointestinal diseases
US9669046B2 (en) 2008-10-24 2017-06-06 Cempra Pharmaceuticals, Inc. Biodefenses using triazole-containing macrolides
US8796232B2 (en) 2008-10-24 2014-08-05 Cempra Pharmaceuticals, Inc. Methods for treating resistant diseases using triazole containing macrolides
US20110195920A1 (en) * 2008-10-24 2011-08-11 Cempra Pharmaceuticals, Inc. Biodefenses using triazole-containing macrolides
US9072759B2 (en) 2008-10-24 2015-07-07 Cempra Pharmaceuticals, Inc. Biodefenses using triazole-containing macrolides
US20110237534A1 (en) * 2008-10-24 2011-09-29 Cempra Pharmaceuticals, Inc. Methods for treating gastrointestinal diseases
US9439918B2 (en) 2008-10-24 2016-09-13 Cempra Pharmaceuticals, Inc. Methods for treating gastrointestinal diseases
US20110201566A1 (en) * 2008-10-24 2011-08-18 Cempra Pharmaceuticals, Inc. Methods for treating resistant diseases using triazole containing macrolides
US9901592B2 (en) 2008-10-24 2018-02-27 Cempra Pharmaceuticals, Inc. Methods for treating resistant diseases using triazole containing macrolides
US9937194B1 (en) 2009-06-12 2018-04-10 Cempra Pharmaceuticals, Inc. Compounds and methods for treating inflammatory diseases
US9480679B2 (en) 2009-09-10 2016-11-01 Cempra Pharmaceuticals, Inc. Methods for treating malaria, tuberculosis and MAC diseases
US8759500B2 (en) 2010-03-22 2014-06-24 Cempra Pharmaceuticals, Inc. Crystalline forms of a macrolide, and uses therefor
US8975386B2 (en) 2010-03-22 2015-03-10 Cempra Pharmaceuticals, Inc. Crystalline forms of a macrolide, and uses therefor
US9051346B2 (en) 2010-05-20 2015-06-09 Cempra Pharmaceuticals, Inc. Process for preparing triazole-containing ketolide antibiotics
US9815863B2 (en) 2010-09-10 2017-11-14 Cempra Pharmaceuticals, Inc. Hydrogen bond forming fluoro ketolides for treating diseases
US10188674B2 (en) 2012-03-27 2019-01-29 Cempra Pharmaceuticals, Inc. Parenteral formulations for administering macrolide antibiotics
US9861616B2 (en) 2013-03-14 2018-01-09 Cempra Pharmaceuticals, Inc. Methods for treating respiratory diseases and formulations therefor
US9751908B2 (en) 2013-03-15 2017-09-05 Cempra Pharmaceuticals, Inc. Convergent processes for preparing macrolide antibacterial agents

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EP0854879B1 (fr) 2002-01-16
AU708351B2 (en) 1999-08-05
UA52621C2 (uk) 2003-01-15
IL123613A0 (en) 1998-10-30
SK43198A3 (en) 1998-11-04
FR2739620B1 (fr) 1997-12-19
GEP20032899B (en) 2003-02-25
PT854879E (pt) 2002-07-31
TR199800624T1 (xx) 1998-06-22
PL326001A1 (en) 1998-08-17
ZA966666B (en) 1997-08-06
EA000765B1 (ru) 2000-04-24
SK283619B6 (sk) 2003-10-07
AR004688A1 (es) 1999-03-10
EA199800280A1 (ru) 1998-10-29
PL183645B1 (pl) 2002-06-28
NO981630L (no) 1998-04-08
RO118874B1 (ro) 2003-12-30
NO981630D0 (no) 1998-04-08
BG102350A (en) 1999-03-31
BR9610959A (pt) 1999-03-02
DK0854879T3 (da) 2002-05-06
CN1067401C (zh) 2001-06-20
DE69618607T2 (de) 2002-08-14
WO1997013774A3 (fr) 1997-05-29
MX9802655A (es) 1998-11-30
AU7220896A (en) 1997-04-30
CZ293430B6 (cs) 2004-04-14
HUP9900136A3 (en) 2000-04-28
NO312592B1 (no) 2002-06-03
KR100451063B1 (ko) 2004-12-17
JPH11513401A (ja) 1999-11-16
BG63752B1 (bg) 2002-11-29
CZ105598A3 (cs) 1998-07-15
EP0854879A2 (fr) 1998-07-29
WO1997013774A2 (fr) 1997-04-17
DE69618607D1 (de) 2002-02-21
SI0854879T1 (en) 2002-08-31
ATE212034T1 (de) 2002-02-15
HUP9900136A1 (hu) 1999-05-28
KR19990064100A (ko) 1999-07-26
CA2231562C (fr) 2006-11-28
CN1199403A (zh) 1998-11-18
ES2171722T3 (es) 2002-09-16
FR2739620A1 (fr) 1997-04-11
EE03878B1 (et) 2002-10-15
JP4327248B2 (ja) 2009-09-09
CA2231562A1 (fr) 1997-04-17
EE9800109A (et) 1998-10-15
AP888A (en) 2000-11-10

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